Reaction #69709

Reaction equation

(2,4-bis-benzyloxy-5-bromo-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone

sodium trifluoroacetate

→

title compound

Yield 29.3%

(2,4-Bis-benzyloxy-5-trifluoromethyl-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone

Yield 29.3%

Conditions

Workup

1. 1
   Otherwere dried under vacuum (0.04 mbar) for 6 hours
2. 2
   OtherThe flask was flushed with nitrogen, DMF (5 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   TemperatureAfter cooling to r.t.
5. 5
   workup.ADDITIONthe mixture was diluted with DCM (100 mL)
6. 6
   Filtrationfiltered through Celite
7. 7
   Washrinsing with DCM
8. 8
   ConcentrationThe filtrate was concentrated to dryness
9. 9
   Otherthe residue was partially purified by flash chromatography on silica (ethyl acetate/petrol gradient, 0-20%)
10. 10
    OtherThe purest fraction was recrystallised from methanol

Procedure

A mixture of (2,4-bis-benzyloxy-5-bromo-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone (491 mg, 0.95 mmol), sodium trifluoroacetate (649 mg, 4.8 mmol) and copper (I) iodide (364 mg, 1.91 mmol) were dried under vacuum (0.04 mbar) for 6 hours. The flask was flushed with nitrogen, DMF (5 mL) was added and the mixture heated at 150° C. for 17 hours. After cooling to r.t., the mixture was diluted with DCM (100 mL) and filtered through Celite, rinsing with DCM. The filtrate was concentrated to dryness and the residue was partially purified by flash chromatography on silica (ethyl acetate/petrol gradient, 0-20%). The purest fraction was recrystallised from methanol to afford the title compound as a white solid (140 mg, 29%). 1H NMR (methanol-d4) 7.60 (1H, s), 7.48-7.44 (2H, m), 7.40 (2H, t), 7.37-7.21 (m, 9H), 7.17 (1H, d), 7.02 (1H, s), 5.29 (2H, s), 5.24 (2H, s), 4.88 (2H, s), 4.62 (2H, s). MS: [M+H]+ 504.

Source